Structure via PubChem · Public domain (PubChem)
rifaximin
Sign in to saveAlso known as Xifaxan, Rifacol, Rifaximinun, Rifamycin L 105, Rifamycin L 105SV, Xifaxsan, Rifaxidin
Rifaximin is a non-absorbable, broad-spectrum antibiotic mainly used to treat travelers' diarrhea. It is based on the rifamycin antibiotics family. Since its approval in Italy in 1987, it has been licensed in more than 30 countries for the treatment of a variety of non-infectious gastrointestinal diseases like irritable bowel syndrome and hepatic encephalopathy. It acts by inhibiting RNA synthesis in susceptible bacteria by binding to the RNA polymerase enzyme. This binding blocks translocation, which stops transcription. It was developed by Salix Pharmaceuticals.
Key facts
- Drug.Verifiedfields
- changed
- Drug.verifiedrevid
- 464382444
- Drug.image
- Rifaximin.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 300
- Drug.image2
- Rifaximin ball-and-stick.png
- Drug.image_class2
- bg-transparent
- Drug.width2
- 300
- Drug.tradename
- Xifaxan, others
- Drug.MedlinePlus
- a604027
- Drug.DailyMedID
- Rifaximin
- Drug.pregnancy_AU
- B1
- Drug.routes_of_administration
- By mouth
- Drug.ATC_prefix
- A07
- Drug.ATC_suffix
- AA11
- Drug.ATC_supplemental
- , ,
- Drug.legal_CA
- Rx-only
- Drug.legal_US
- Rx-only
via Wikipedia infobox
Chemical data
- Formula
- C43H51N3O11
- Molecular weight
- 785.9 g/mol
- IUPAC name
- [(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-2,15,17,36-tetrahydroxy-11-methoxy-3,7,12,14,16,18,22,30-octamethyl-6,23-dioxo-8,37-dioxa-24,27,33-triazahexacyclo[23.10.1.14,7.05,35.026,34.027,32]heptatriaconta-1(35),2,4,9,19,21,25(36),26(34),28,30,32-undecaen-13-yl] acetate
- SMILES
- C[C@H]1/C=C/C=C(\C(=O)NC2=C(C3=C(C4=C(C(=C3O)C)O[C@@](C4=O)(O/C=C/[C@@H]([C@H]([C@H]([C@@H]([C@@H]([C@@H]([C@H]1O)C)O)C)OC(=O)C)C)OC)C)C5=C2N6C=CC(=CC6=N5)C)O)/C
- InChIKey
- NZCRJKRKKOLAOJ-XRCRFVBUSA-N
- XLogP
- 6.9
- Polar surface area
- 198 Ų
- H-bond donors
- 5
- H-bond acceptors
- 12
- Formal charge
- 0
via PubChem
Research
2,112 papers- Review of rifaximin as treatment for SIBO and IBS.Expert opinion on investigational drugs · 2009
- Rifaximin treatment in hepatic encephalopathy.The New England journal of medicine · 2010
- Combination therapy with rifaximin and lactulose in hepatic encephalopathy: A systematic review and meta-analysis.PloS one · 2022
- Rifaximin-mediated gut microbiota regulation modulates the function of microglia and protects against CUMS-induced depression-like behaviors in adolescent rat.Journal of neuroinflammation · 2021
- Rifaximin and alternative agents in the management of irritable bowel syndrome: A comprehensive review.Archiv der Pharmazie · 2024
via PubMed
~10 min read
Encyclopedic overview
15 sectionsContents
- Medical uses
- Travelers' diarrhea
- Irritable bowel syndrome
- ''Clostridioides difficile'' infection
- Hepatic encephalopathy
- Other uses
- Veterinary uses
- Special caution
- Side effects
- Interactions
- Pharmacology
- Mechanism of action
- Availability
- Physicochemical properties
- References
Rifaximin is a non-absorbable, broad-spectrum antibiotic mainly used to treat travelers' diarrhea. It is based on the rifamycin antibiotics family. Since its approval in Italy in 1987, it has been licensed in more than 30 countries for the treatment of a variety of non-infectious gastrointestinal diseases like irritable bowel syndrome and hepatic encephalopathy. It acts by inhibiting RNA synthesis in susceptible bacteria by binding to the RNA polymerase enzyme. This binding blocks translocation, which stops transcription. It was developed by Salix Pharmaceuticals.
== Medical uses == === Travelers' diarrhea === Rifaximin is used to treat travelers' diarrhea caused by E. coli bacteria in people aged twelve years of age and older. It treats travelers' diarrhea by stopping the growth of the bacteria that cause diarrhea. Rifaximin will not work to treat travelers' diarrhea that is bloody or occurs with fever.
Excerpted from Wikipedia’s “rifaximin” article, available under the CC BY-SA 4.0 licence.